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$1,399,000
616964 MLS
Discover a rare opportunity in the heart of Duck Key at 1 Trinidad Street — a premier parcel spanning over an acre in one of the most desirable neighborhoods in the Florida Keys. This exceptional property offers remarkable potential for new construction, redevelopment, or long-term investment. With its generous size, privacy, and prime location directly across from the Duck Key Clubhouse — and just steps from the pool, tennis courts, and social amenities — this site combines lifestyle appeal with investment value. Whether you're envisioning a luxury Keys estate, a multi-structure retreat, or a strategic hold for future growth, the possibilities are endless. The property carries density for up to 7 homes, and according to Monroe County, it aligns with the majority of criteria required for ROGO (Rate of Growth Ordinance) building right transfers. While formal approval must follow the county's established process, preliminary guidance supports the feasibility of securing those rights — offering a compelling path for developers and investors. Large parcels of this caliber are increasingly rare — build your vision and create something extraordinary on Duck Key.

1 Trinidad St, Duck

$875,000
2 Beds 2 Baths 617494 MLS
If you need more dockage than most half duplexes in Key Colony Beach, here it is. This property offers an impressive 42 feet of dockage with a concrete seawall and wooden step-down dock, ready for your big boat and all your water toys. Exceptionally maintained by the same family for over 40 years, this home shows true pride of ownership from the moment you enter the open-concept kitchen, dining and living area. A large impact slider and picture window fill the space with natural light and frame beautiful views of the 100 foot wide canal. These refreshing water views invite you onto the covered porch, ideal for entertaining, outdoor dining or simply relaxing and enjoying the island lifestyle. Boaters, anglers, divers and nature lovers will appreciate the brief 5 minute cruise to both the open ocean and the open gulf. The location also offers excellent proximity to major airports including 10 to 15 minutes to Marathon International, just over an hour to Key West International, 2 hours to Miami International and 2.5 hours to Fort Lauderdale International. Key Colony Beach is known as the gem of the Florida Keys and features a 15 street island layout perfect for biking along with pickleball, golf, a marina, three playgrounds, bocce ball, horseshoes, a post office, three restaurants and iconic Sunset Park. Paradise is waiting for you here and this island lifestyle can be yours.

261 9th St, Key Colony

$799,000
3 Beds 2 Baths 616898 MLS
Welcome to 91 Sirius Lane, a beautifully remodeled canal-front retreat in the heart of Geiger Key's sought-after Tamarac Park, an established boating community just 15 miles outside of Key West. This 2-bedroom + bonus Den/3rd Bedroom and Florida Room, 2 Bath home offers 1,404 sq ft of updated living space on a 5,850 sq ft lot with 45 feet of concrete dockage. Boaters will love the fantastic deep water ocean access with no bridges and just moments to the open sea. Step inside to a bright and open floor plan featuring new luxury vinyl tile flooring and a stunning kitchen with sleek gray cabinetry, white quartz countertops, and stainless appliances. The adjacent laundry room/pantry adds convenience, while the expansive living and dining areas flow seamlessly to the covered porch overlooking the water. Outside, unwind beneath swaying palms in your private tropical paradise. Enjoy the bamboo outdoor shower, entertain on the spacious new deck, or fish from your dockside table as the sun sets over the water. This move-in-ready home combines laid-back Keys charm with modern updates. Offered furnished and ready for a full-time residence, vacation getaway, or investment.

91 Sirius Ln, Geiger

$719,000
1 Beds 2 Baths 615004 MLS
This oceanfront residence offers breathtaking, unobstructed ocean views. Fully furnished with brand-new décor, the unit is truly move-in ready. The first level features an open-concept living and kitchen area, along with a half bath. Upstairs, the ocean-view bedroom includes a second full bathroom. Private balconies on both levels provide the perfect setting to relax while enjoying spectacular ocean views and refreshing island breezes. Additional highlights include a newly installed private elevator for added convenience. Community amenities are exceptional, featuring an expansive resort-style pool, a newly updated marina, fish-cleaning stations, outdoor grilling areas, tiki huts, and a beautifully appointed clubhouse ideal for entertaining family and friends. Owners also enjoy access to a private boat ramp, with boat slips available based on availability. Located within a secure, gated community, this condominium is ideal as a full-time residence, vacation retreat, or investment opportunity. Offering luxury, comfort, and unparalleled waterfront access, this property delivers the ultimate Florida Keys lifestyle.

10877 Overseas Hwy Unit Unit 81, Marathon

$4,900,000
1 Beds 3 Baths 613251 MLS
Once-in-a-Lifetime Opportunity: Own the Iconic Alabama Jacks in Key Largo! Step into the legacy of one of the most celebrated waterfront establishments in the USA. This legendary bar and restaurant, continually rated among the Best Bars & Restaurants in South Florida, Florida, and the nation, is ready for its next chapter. Located on Card Sound Road at the foot of the Card Sound Bridge, Alabama Jacks has been a beloved destination since the 1950s, renowned for its authentic charm, lively atmosphere, and world-famous conch fritters. Key Features: Rich History: Established in 1947 and operated by the current owner since 1981, this landmark has maintained its iconic status and rustic charm, drawing locals, tourists, and celebrities alike. Turnkey Package: Sale includes the business name, domain names, Facebook page, a thriving retail t-shirt business, proprietary recipes, and all furniture, fixtures, and equipment (FF&E). Prime Waterfront Property: Two parcels totaling 41,602 square feet (.95 acres) with over 360 linear feet of boat docks, direct boating access, and a private boat ramp (currently unused, offering potential for new revenue streams). Buildings & Infrastructure: Includes 2,297 sq. ft. of finished space, 4,729 sq. ft. of canopy space, and an apartment for onsite living or staff use. Also features a desalination system and a backup water truck with a tank. Long-Term Lease: New & Secure, 20-year lease with the U.S. Government renewed in 2021 through 2041. Unparalleled Legacy Alabama Jacks is a true piece of Americana, beloved by generations and celebrated in publications and TV appearances by icons like Emeril Lagasse, Conde Nast, and Kathie Lee Gifford. Whether you're continuing its proud traditions or exploring new opportunities, this business is primed for success. Opportunity to Franchise the name and brand. Don't miss this chance to own a slice of Florida Keys history and elevate an already thriving landmark to its next level.

58000 Card Sound Rd, Key Largo

$1,150,000
2 Beds 3 Baths 618751 MLS
Tucked away in the heart of Old-Town Key West! Welcome to 1075 R10 Duval Street offers the perfect blend of privacy, island charm, and effortless living. This thoughtfully designed 2-bedroom, 2.5-bathroom residence features 1,240 square feet of living space and is ideally positioned in a quiet, off-the-street setting while remaining just moments from shopping, dining, beaches, Boating and all that makes Key West extraordinary. Inside, you'll find a bright and inviting layout filled with natural light, and an easy indoor-outdoor flow. The guest bedroom has an en suite bathroom, perfect for friends and family. The spacious living and dining areas open seamlessly to a private outdoor space--perfect for morning coffee, evening cocktails, or soaking up the tropical breeze. A convenient half bath on the main level makes entertaining easy and comfortable for guests. The well-appointed kitchen offers ample cabinetry and workspace, making hosting effortless. Upstairs, two generously sized bedrooms each feature their own en-suite bathrooms, creating ideal separation and privacy for owners and guests alike. Primary/master bedroom has vaulted ceilings, private balcony and a walk in closet, fit for any King or Queen of the house. Step outside and enjoy your own private island setting, surrounded by lush landscaping that creates a peaceful and inviting atmosphere. Amazing Pool that over looks Duval Street. Watch the day go by or watch a parade from the roof top pool. Located within the Transit Receivership Zone (please note this unit does not currently hold a transit license), the property offers flexibility for a variety of ownership goals while remaining compliant with local regulations. Private. Peaceful. Perfectly Key West.

1075 Duval St Unit R10, Key West

$1,849,000
3 Beds 3 Baths 617599 MLS
Reduced $100k! Sturdy & stunning!. Enter into a bouquet of large impact windows w/10' ceilings throughout. Well appointed with luxurious finishes & 3 large patios. Built to withstand the unknown w/ concrete walls & roof. This 3 bed 2 1/2 bath canal front (Oceanside) home has never been lived in. Be the first to enjoy sunrises & sunsets from your choice of 3 patios over 2 floors of living space. This spacious home offers a large open kitchen w/balcony access for entertaining, Master suite w/ balcony access and incredible sunsets, an extravagant master bath,an additional entertainment/family room, wet bar, laundry room, elevator, private dock & more. Room for a pool. Total Sq footage is 5875 Sq ft, This peaceful paradise is situated in the quaint well established Oceanside Harborage community! Hop on your boat from your 41' private doc & be in the Ocean/Sandbar in less than 5 mins! The Harborage is a quaint beautiful, 2 street community known for its deep water. Maintenance includes yard, clubhouse w/waterfront pool, ice machine, laundry, boat ramp, boat trailer storage, good vibes and best of all LOCATION! Seller Financing is an option. A pleasure to show..

84 Coral Way Unit -=, Key Largo

$999,000
3 Beds 3 Baths 612215 MLS
Enjoy unparalleled flexibility and luxury with this transient-licensed 3-bedroom, 3-bathroom condo, an exceptional opportunity for a personal coastal escape or a versatile vacation rental. Fully furnished with modern decor, high-end appliances, and meticulous craftsmanship, this turnkey property is poised to impress from the moment you step in. Conveniently located at the entrance to the island of Key West, it offers seamless access to a wealth of shops, dining, entertainment, and recreation options, delivering convenience and enjoyment at every turn. With its streamlined rental setup, this condo is perfect for buyers seeking potential income or for those desiring an upscale island retreat all to themselves with all the amenities one could possibly ask for. Property has two restaurants, a bar, covered parking, mini marina dockage for boating while visiting and a fitness center all on site. Experience the best of refined island living!

3841 N Roosevelt Blvd Unit 222, Key West

$1,850,000
2 Beds 2 Baths 617440 MLS
Open water pool home with breathtaking views of Bogie Channel and direct deep water access to both the Atlantic Ocean and the Gulf. Located on a spacious 13,275 sq ft lot, this solid concrete ground-level residence is a true boater's paradise featuring a 75-foot concrete dock and a protected boat basin. Inside, the 1,980 sq ft home offers a large great room, a Florida Room perfect for sunrise coffee, and a spacious kitchen with quartz countertops and a center island ideal for entertaining. Enjoy the seamless indoor-outdoor lifestyle with a waterfront pool surrounded by tropical landscaping, swaying palms, and a peaceful outdoor patio. The primary suite offers views of the pool and water, blending luxury and tranquility. Built to last with impact-resistant doors and windows and a durable metal roof. Additional features include a one-car garage, beautifully manicured grounds, and regular visits from native birds and Key Deer. Ride your bike across the bridge to No Name Key or walk to the world-famous No Name Pub. Just minutes to shopping, dining, and all the Lower Keys have to offer.

1607 Sunrise Dr, Big Pine

$665,000
2 Beds 3 Baths 617627 MLS
Nestled just steps away from the Hawks Cay Resort Sunset Pool and the stunning ocean waters, this charming two-story townhouse offers the perfect blend of comfort and style. Discover the unique charm of Key West style architecture and experience the beauty of this pool front townhome. Featuring fresh interior paint, this home boasts a newly installed white quartz kitchen countertop that perfectly complements the white cabinets, stainless steel appliances, and updated main level flooring. This villa boasts two comfortably sized bedrooms, each with its own balcony. The primary suite overlooks the lush greenery of the Sunset Pool, offering peek-a-boo water views and an ensuite bathroom. An additional full bathroom is located in the upstairs hallway, while a convenient half bath can be found on the first level. This property is completely turnkey if you desire to manage it independently. Hawks Cay Resort offers an optional onsite management program with a complimentary club membership for their participants, allowing owners to enjoy all of the amenities offered throughout the property. Experience a resort lifestyle at its finest with this exquisite property. Don't miss your chance to make it your own!

5081 Sunset Village Dr, Duck Key

$998,000
1 Beds 1 Baths 618122 MLS
Step into a piece of Old Town Key West history. Built in 1928, this storybook Old Town cottage captures everything to love about Key West including its timeless character and that easy island rhythm you can feel the moment you arrive. Light, bright, and beautifully furnished, it's move-in ready, the perfect turn-key retreat for anyone dreaming of a second home or an easy vacation rental in the heart of Key West. Inside, you'll find soaring wood-vaulted ceilings and warm floors features that hint to island's past. The airy loft adds extra space and character, while the private back deck invites unforgettable evenings dining under the stars. Out front, the iconic porch is made for slow evenings, and people-watching ... the classic Key West pastime. Just two blocks from Duval Street, this location is unbeatable, it's close enough to walk to the best restaurants, galleries, and shops, yet tucked away for peace and privacy. Even better, it's in the coveted X-Zone, so no flood insurance is required, and yes, it has its own, coveted off-street parking spot This isn't just a home, it's a private oasis. It's YOUR Key West story waiting to be written.

817 Terry Ln, Key West

$24,995,000
5 Beds 8 Baths 617705 MLS
Newly completed private oceanfront estate on 2+ acres in Plantation Key, offering an extraordinary combination of scale, privacy, dockage, and resort-style living in the heart of the Florida Keys. Designed for luxury coastal living, entertaining, and extended stays, this exceptional estate features over 9,000 sq. ft. of interior living space and more than 15,000 sq. ft. under roof. Set behind a gated entry, the residence offers 5 ensuite bedrooms, 5 full baths, 3 half baths, multiple flex spaces, an elevator, expansive covered porches, and seamless indoor-outdoor living. Additional luxury spaces include an in-home theater, private gym, and a massive office overlooking the ocean, all of which could easily serve as additional bedrooms, creating the potential for an 8-bedroom layout. The outdoor spaces are designed to showcase the Atlantic Ocean setting, with a resort-style pool, jacuzzi, generous lounging areas, and sweeping oceanfront views. Boaters will appreciate the 80-ft dock, 20,000 lb boat lift, and 160-ft jetty, creating outstanding access for enjoying the Keys lifestyle. With vacation rental zoning, the property also offers investment flexibility for those seeking personal use, income potential, or a legacy estate. Private oceanfront acreage of this scale is increasingly rare in the Upper Keys, making 87895 Old Hwy a standout opportunity for the buyer seeking a newly completed Florida Keys estate with privacy, presence, flexible living space, and exceptional waterfront amenities.

87895 Old Hwy, Islamorada

$750,000
3 Beds 2 Baths 613083 MLS
All NEW NEXT TO MARINA & POOL Stunning Islamorada 3 full bedrooms 2 brand new bathrooms plus oversized loft with additional queen and three twin beds. This Townhouse has ALL NEW kitchen, new bar, new built-ins, new custom fishing closet & storage, brand new 4 ton AC unit, 2 brand new Bathrooms with showers, new extended loft area, new full size Washer/Dryer, new BBQ area with new patio chicago brick pavers plus private patio shaded area with beautiful palms trees, serena & lily furniture inside, new electric panel, new electric water heater, new 80' smart OLED TV, new area just for refreshments, coffee and bar, new 4 ton AC unit, high end hurricane impact windows and doors that are reflective and cannot see inside. New Electric car charging electric panel exclusive to this unit. Best area in the community next to pool and marina with two pickleball courts and basketball court in the rear. Sleeps easily over 10 people. King bed in the master bedroom, 2 queen mattress in additional bedroom and loft along with 5 twin mattresses. Rented in winter for over $6,500 a month! Call today! This community features a new private beach, marina, dock and clubhouse. Being SOLD fully furnished and fully equipped with high end appliances (FRIGIDAIRE), high end furniture (SERENA & LILY) and furnishings. See 3 Videos: https://youtu.be/P8cOME8P_kY; https://youtu.be/b6RmPMU8pvk; https://youtube.com/shorts/BEo0F_YzVFE;

87200 Overseas Hwy Unit V9, Islamorada

$4,300,000
4 Beds 6 Baths 617513 MLS
**31 photos have been virtually staged and enhanced to assist buyers in visualizing design and decor options for this home.** Casa Sapodilla introduces itself with the kind of presence that feels both storied and serene. Built in 1996 and set at 13' elevation on Solares Hill, the residence pays homage to the architectural romance of Old Town's most celebrated homes.. broad verandas, intricate trim work, and Brazilian Cherry hardwood floors that recall a bygone era of island craftsmanship. Inside, the home unfolds in layers of refinement. Sunlit rooms connect gracefully to the outdoors through French doors and deep porches. The main house's split-level design elevates the primary suite with its own private staircase, while two additional bedrooms ascend another, creating a sense of calm seclusion. A separate pool suite, complete with private entrance, extends the home's versatility. The kitchen is anchored by a suite of premier appliances.. including a new SubZero refrigerator and a refurbished Viking gas range, and framed by custom cabinetry and built-ins. Recent upgrades such as the 2025 metal roof, updated HVAC systems, and a 24 kW Generac whole-house generator reflect meticulous stewardship. Outside, the grounds rise to the level of a private resort. Tropical gardens wind around stone pathways, illuminated at night by soft landscape lighting. A heated saltwater lagoon-style pool, resurfaced in 2025, curves around natural rock formations, a spa, and three cascading waterfalls. Every vista offers a moment of stillness.. from the shaded verandas to the courtyard designed for open-air dining. A one-car air-conditioned garage, currently serving as an art studio, and a two-car driveway complete the thoughtful layout. Just blocks from Duval Street and the Key West Historic Seaport, Casa Sapodilla is both connected and deeply private.. a luxury retreat rooted in island elegance.. Inquire within for details on the low insurance costs available for this home

600 Elizabeth St, Key West

$1,275,000
2 Beds 2 Baths 618511 MLS
This show-stopping luxury condo delivers a rare blend of historic charm with a fully renovated interior that was just completed a few years ago. The first level features an open living and dining plan with 10' ceilings, an abundance of natural light, restored Dade County Pine accent walls, plantation shutters, modern lighting, and tile flooring throughout. The kitchen was built to impress and features a large quartz island, Cafe Collection appliances, a gas range, designer tile backsplash, and a separate coffee and cocktail bar. Practical touches include an entry way storage closet, built-in closet systems, and a full-size GE washer and dryer tucked neatly under the stairs. The upstairs primary suite feels like a private retreat.. it features a sitting area with double French doors that open to the balcony perch where you'll enjoy views of beautiful sunsets through the treetops. The en suite bath is finished with gorgeous Onyx Style slab tile, a double vanity, designer fixtures and a glass shower with statement detailing. This luxury condo is offered fully furnished and turnkey, with local Key West history woven throughout. 30-day rentals are allowed with restrictions, it's in the X Flood Zone, and from here it's always an easy stroll to Fort Zach Beach, Truman Waterfront Park, and the Duval Street corridor for fine dining, shopping, and live entertainment, capturing the ease and energy of Key West living..

927 Thomas St Unit #2, Key West

$1,595,000
3 Beds 3 Baths 618272 MLS
Priced at Current appraised value, this 3-bedroom, 3-bath concrete fortress on deep water canal (5' draft) is located in the highly sought-after Summerland Cove with quick access to both the Gulf and Atlantic--just a 15-minute boat ride to open ocean--this home is a true boater's paradise. Additionally, enjoy Airstrip rights as part of the Summerland Airport community. Set on a generous 75' x 100' corner lot, the property offers exceptional dockage, thoughtful upgrades, and wonderful potential to further customize your Keys dream home. Designed for the boating lifestyle with room for a POOL featuring: • A 50' wide deep-water canal allows for larger boats • 15,000 lb boat lift, two-8,000 lb davits, and 75 ft seawall with swim ladder • A concrete boat launch that has been decked for easy access. • Covered Parking for 5 vehicles with a three-bay carport + Garage / Living space with full bath and 11' ceiling height • RV Parking for large RV with 45' concrete runners • A 75' x 100' corner lot with plenty of room for a pool Pull in the carport protected from the rain and bring your groceries up the inside stairwell. Inside, you'll find a welcoming blend of coastal charm and modern updates: • Renovated kitchen with stainless steel appliances and built in double drawer freezer • Air-conditioned screened porch with sunrise views • Built-in propane pizza oven -- perfect for entertaining • New water heater (2025), new epoxy walkway flooring (2025), and unique aluminum railings (2025) • Recent exterior paint, metal roof (2018) * hurricane impact windows *Garage/Living space with new epoxy flooring • Airport community As a final bonus, a Key West 244 Bluewater center console with 250 Suzuki is available for purchase -making it even easier to step straight into the Keys boating lifestyle. This is a rare opportunity to own a beautiful home in one of the Lower Keys' most desirable neighborhood. *Owner financing will be considered Se

887 Bay Dr, Summerland

$763,000
4 Beds 2 Baths 618615 MLS
If you want a spacious home with plenty of privacy, this property delivers. Set within a lushly landscaped 12,500 sq. ft. double lot, the 2,136 sq. ft. living area provides ample space for family and guests with 4-bedrooms, 2-baths, a family room, laundry room and additional room that could be a 5th bedroom. Refreshing colors complement the space, and the tasteful furnishings are included with just a few exceptions. You can literally move in with only your suitcase! Central A/C cools and heats the majority of the home, and mini-split units cover the rest. Flooring consists of solid bamboo and tile throughout. The fenced back yard features a tiki hut for entertaining and relaxing. The property is bordered on two sides by county and state-owned protected lands, adding to the privacy. The detached garage is a bonus!

30374 Oleander Blvd, Big Pine

$1,950,000
3 Beds 3 Baths 616756 MLS
This stately concrete home has all the best of everything on one of the best boating areas in the Lower Keys Thís home is being offered completely furnished with electronics & most of the artwork, All kitchen and bedding items. The large great room has lots of seating. with soaring ceilings and lots of natural light. The kitchen is a chef's delight with sub zero appliances and induction chef's range. Lots of cabinets and extra storage The master bedroom with in suite bath is exquisite. Top of the line soft and comfy mattress and 45'' flat screen TV. 2nd bedroom also has it's own private bath for the extra guests. Kick back and relax on the oversized screened porch or hang out under the shaded Tiki hut dockside. Nice ocean view from dock level. 2nd screen patio area at dockside completes the package. For the anglers you will love the fish cleaning station, boat lift, 1 floating dock and bait freezer to make those daily fishing trips a breeze. Boating access is super with full 4'draft to accommodate the larger fishing vessels. Excellent short term rental history for extra income!! This is a must see!!!

860 Lagoon Dr, Summerland